A landscape is a palimpsest of the interactions between human activities and ecological dynamics. In an interdisciplinary perspective of dialogue between the ‘Two Cultures’ (Natural Sciences and Humanities), a study of a rural area has been carried out through a reading of plant ecosystems as signs of human impact. The purpose of this paper—as part of the project ‘Harvesting Memories’: Ecology and landscape archaeology of Castro/Giardinallo Valley and Mt. Barraù district (Corleone, Palermo, Sicily)—is to analyse the formative-processes of a Sicilian rural landscape and its changes in the last century. A key element in the reconstruction of the formation of the present landscape is the series of vegetation types which indicate the successive stages of different plant communities occurring in close relation with the human exploitation of natural resources (forestry, grazing, agriculture). An analytical frame for the landscape’s biography was generated through a diachronic comparison of images of the area in 1955 and the present day. The comparison in GIS of both spatial and typological changes in the different vegetation series, together with the calculation of a naturalness index Naturalness Evaluation Index, showed the trajectory the landscape (‘landscape-change map’) has undergone since the 1950s, with an increase in wooded and shrubbed areas and a reduction of pastures and cultivated areas.